The Epstein Diaries #8: Epstein Goes to Jail—For the First Time

But a decades-long, bitterly contested legal battle is just beginning.

Photo illustration by Eric Faison/The Daily Beast

He has turned down the offer of a misdemeanor and a slap on the wrist, and is now, instead, facing the possibility of a life sentence. In the eighth installment of the Epstein Diaries, Jeffrey Epstein and his legal dream team wrangle out of the most serious immediate consequences only to fall into a bottomless pit of legal settlements, a slippery slope of conspiracy theories, and an ultimately mortal legal battle—the World vs. Jeffrey Epstein.

Context is everything. Revisit where we left off in the previous installment, The Epstein Diaries #7: From ‘Bad Boy’ to Trafficker.

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As the federal government threatened to indict him on sex trafficking charges—and to hold him indefinitely, because trafficking is one of the few crimes with a presumption against bail—Epstein certainly regarded himself to be in a Kafkaesque situation. He was also jaunty about it.

I saw him perhaps four or five times during the 2006-2008 period, usually for tea at his house in New York City, in front of the baronial fireplace. I had never known anyone to be the subject of a sex crimes investigation and was, I confess, a curious witness to how he would handle this disgrace and humiliation.

He was matter-of-fact, blithe, incapable of not making a joke about his situation, and as well, resigned to people not understanding or refusing to accept the nature of his desires. (“I’d be in much better shape if this were a gay thing.”) But he was also a general in command. He coolly laid out the field of play: the various characters both in Palm Beach and in the Justice Department; the legal maneuvers on his part and against him; his dream-team lineup of lawyers; and a defense of his own position. It was quite a Clintonesque equivocation: He did not have sex, he never had sex, he didn’t like sex—that is, penetrative sex. He only liked hand jobs.

In the Room with Jeffrey Epstein

A by-product of his command-and-control attitude—that the force arrayed against him demanded an equal or greater force against it—meant he was spending more money than any other criminal sex defendant had ever spent in the state of Florida, producing a gusher of cash for the lawyers he kept hiring.

The outcome of the case—the way-too lenient outcome, in the favored telling—would come to be seen as the result of the nefarious influence that Epstein’s money and power were able to summon. And he certainly was trying to summon any he could. But money, at this level, affects everything. The system is transformed by it, and not just in his favor. Jeffrey Epstein created his own legal ecosystem, enriching his lawyers and, ultimately, much of the South Florida bar. The money was a variable that tilted almost every factor both for him and against him.

He had a specific model here: his former friend, and now nemesis, Donald Trump. Among all that Epstein derided Trump for, one thing he admired was Trump’s striking ability to get out of a jam—to beat the system at its own game.

But so far, Epstein’s efforts only seemed to get him into a deeper jam—from a local prosecution in Palm Beach now to the weight of the federal government on him.